N,N'-Dimethylethylenediamine → (R)-4-tert-butyl-3-{4-[4-(2,4-dimethylphenyl)piperazine-1-carbonyl]phenyl}oxazolidin-2-one

HRID 1804149

Reaction equation

HRID 1804149 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([C:15]([C:17]2[CH:22]=[CH:21][C:20](I)=[CH:19][CH:18]=2)=[O:16])[CH2:11][CH2:10]1.[C:24]([C@@H:28]1[CH2:32][O:31][C:30](=[O:33])[NH:29]1)([CH3:27])([CH3:26])[CH3:25].C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I.O.C1(C)C=CC=CC=1>[C:24]([C@@H:28]1[CH2:32][O:31][C:30](=[O:33])[N:29]1[C:20]1[CH:21]=[CH:22][C:17]([C:15]([N:12]2[CH2:13][CH2:14][N:9]([C:3]3[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=3[CH3:1])[CH2:10][CH2:11]2)=[O:16])=[CH:18][CH:19]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 2734860(4R)-4-tert-Butyl-1,3-oxazolidin-2-oneHCID 58484733[4-(2,4-Dimethylphenyl)piperazin-1-yl](4-iodophenyl)methanone

Product 1

HCID 67381127(R)-4-tert-butyl-3-{4-[4-(2,4-dimethylphenyl)piperazine-1-carbonyl]phenyl}oxazolidin-2-oneYield 1.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a mixture of [4-(2,4-dimethylphenyl)piperazin-1-yl](4-iodophenyl)methanone (841 mg) described in Preparation Example 8, (R)-(+)-4-tert-butyloxazolidin-2-one (214 mg), potassium carbonate (553 mg) and copper (I) iodide (76 mg) were added toluene (2 mL) and N,N′-dimethylethylenediamine (100 μL), and the mixture was refluxed for 8 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (chloroform:methanol) to give the title compound (7 mg).

Workup

  1. temperaturethe mixture was refluxed for 8 hr
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-fcb9e87eeb9e440ab812b4e634db72cd
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Linked notes

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